Like all settlements, Winfrith Newburgh shaped and was shaped by the local network of communications.
The earliest track through the village (marked in blue on the map above) was that from Poxwell, which followed the ridge eastwards past the Five Marys above East Chaldon, came down to the village via Colehill Drove and then headed either east to Wool or north across the heath in the direction of Bere Regis. This is certainly prehistoric in origin, and up to the eighteenth century formed the main highway to Weymouth before being superseded by the road in the valley to the north that is now the A352 (shown in red on the map above).
A number of tracks led, and still lead, both northwards onto and across the heath, and south to join the track that paralleled the coast (marked green on the map above). These tracks were used by smugglers such as Charles Weeks, who is said to have lived in the village around 1720 and made Winfrith a ‘general receptacle for smugglers and carriers, who carry off runned goods, the whole parish employed in that way more or less’.
In medieval times the road from Dorchester to Wool, the present A352 , came through Winfrith Newburgh (see red dotted line on the map above) past the end of Thornicks, across the Win by the Pound, up School Lane and past Shilling Plot, but in the eighteenth century, when the road was a turnpike, i.e.one on which a charge was made to travel, a new link was made past the present Red Lion which effectively bypassed the village.